Water as a Direct Proton Source for Asymmetric Hydroarylation Catalyzed by a Rh(I)-Diene: Access to Nonproteinogenic β2/γ2/δ2-Amino Acid Derivatives

A highly enantioselective rhodium-catalyzed intermolecular hydroarylation of alpha-aminoalkyl acrylates using water as a direct proton source has been realized by employing a chiral bicyclo[3.3.0] diene ligand, allowing efficient access to a broad range of alpha-aryl-methyl-substituted beta(2)-, gamma(2)-, and delta(2)-amino esters with excellent enantioselectivities (up to 98% ee) under exceptionally mild conditions. By utilizing this method, a series of structurally interesting benzo-fused heterocyclic molecules and the corresponding beta(2)-, gamma(2)-, and delta(2)-amino acids are facilely constructed.

Automated summary

This study achieves a highly enantioselective rhodium-catalyzed intermolecular hydroarylation of alpha-aminoalkyl acrylates using a chiral bicyclo[3.3.0] diene ligand, leading to a broad range of alpha-aryl-methyl-substituted beta(2)-, gamma(2)-, and delta(2)-amino esters with excellent enantioselectivities (up to 98% ee) under mild conditions. This method provides a new pathway for constructing structurally interesting benzo-fused heterocyclic molecules and the corresponding beta(2)-, gamma(2)-, and delta(2)-amino acids.